1-(4-Nitro­phen­yl)-2-(3-phenyl­allyl­idene)hydrazine

Bao, F.-Y.

doi:10.1107/S1600536808021429

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1531

doi:10.1107/S1600536808021429

Open

access

1-(4-Nitrophenyl)-2-(3-phenylallylidene)hydrazine

Feng-Yu Bao ^a ^*

^aDepartment of Applied Chemistry, College of Sciences, Henan Agricultural University, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: bfyu2008@yahoo.com.cn

(Received 3 July 2008; accepted 10 July 2008; online 19 July 2008)

In the title compound, C₁₅H₁₃N₃O₂, the nitrobenzene and benzene rings make a dihedral angle of 9.1 (2)°. The crystal structure is consolidated by intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Okabe et al. (1993 ).

Experimental

Crystal data

C₁₅H₁₃N₃O₂
M_r = 267.28
Monoclinic, P c
a = 6.1011 (3) Å
b = 12.4505 (6) Å
c = 9.0076 (4) Å
β = 93.273 (3)°
V = 683.12 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 (2) K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.980, T_max = 0.982
5992 measured reflections
1502 independent reflections
783 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.101
S = 0.94
1502 reflections
185 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.89 (3)	2.20 (3)	3.082 (4)	169 (3)
Symmetry code: (i) $[x-1, -y+2, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021429/hg2421sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021429/hg2421Isup2.hkl

checkCIF report

Comment top

4-Nitrophenylhydrazine has applications in organic synthesis and some of its derivatives have been shown to be potentially DNA-damaging and mutagenic agents (Okabe et al., 1993). As part of our interest in the study of the coordination chemistry, we report the synthesis and crystal structure of the title compound (I).

The 4-nitrophenyl group and the benzene ring are slightly twisted, making a dihedral angle of 9.1 (2)°. The dihedral angle between the N1/O1/O2 and its attached benzene ring is 7.4 (2)° (Fig. 1).

The molecules are linked by N—H···O hydrogen bonds to form a zigzag like chain (Fig. 2).

Related literature top

For related literature, see: Okabe et al. (1993).

Experimental top

4-Nitrophenylhydrazine (1 mmol, 0.153 g) was dissolved in anhydrous methanol and H₂SO₄ (98% 0.5 ml) was added. The resultant solution was stirred for several minutes at 351 K. Cinnamaldehyde (1 mmol 0.132 g) in methanol (8 ml) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized in dichloromethane. Brown single crystals of (I) were obtained after 6 d.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. the ORTEP plot of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radii.
	Fig. 2. Packing of (I), showing the intermolecular hydrogen bonds as dashed lines.

1-(4-Nitrophenyl)-2-(3-phenylallylidene)hydrazine top

Crystal data top

C₁₅H₁₃N₃O₂	F(000) = 280
M_r = 267.28	D_x = 1.299 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 1143 reflections
a = 6.1011 (3) Å	θ = 2.1–25.6°
b = 12.4505 (6) Å	µ = 0.09 mm⁻¹
c = 9.0076 (4) Å	T = 296 K
β = 93.273 (3)°	Block, brown
V = 683.12 (6) Å³	0.23 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1502 independent reflections
Radiation source: sealed tube	783 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.980, T_max = 0.982	k = −14→15
5992 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0488P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
1502 reflections	Δρ_max = 0.09 e Å⁻³
185 parameters	Δρ_min = −0.10 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (6)

Crystal data top

C₁₅H₁₃N₃O₂	V = 683.12 (6) Å³
M_r = 267.28	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 6.1011 (3) Å	µ = 0.09 mm⁻¹
b = 12.4505 (6) Å	T = 296 K
c = 9.0076 (4) Å	0.23 × 0.20 × 0.20 mm
β = 93.273 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1502 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	783 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.982	R_int = 0.045
5992 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	3 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.09 e Å⁻³
1502 reflections	Δρ_min = −0.10 e Å⁻³
185 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.0954 (5)	0.9273 (2)	−0.0961 (4)	0.1019 (9)
O2	1.0374 (5)	1.0780 (3)	0.0100 (3)	0.1053 (11)
N1	0.9922 (5)	0.9832 (3)	−0.0132 (3)	0.0768 (9)
N2	0.2734 (4)	0.8124 (2)	0.2572 (3)	0.0689 (8)
N3	0.1907 (4)	0.7139 (2)	0.2171 (3)	0.0718 (8)
C1	0.8094 (5)	0.9377 (3)	0.0590 (4)	0.0595 (8)
C2	0.7374 (5)	0.8364 (3)	0.0209 (4)	0.0663 (10)
H2	0.8096	0.7967	−0.0488	0.080*
C3	0.5603 (5)	0.7940 (3)	0.0852 (4)	0.0644 (9)
H3	0.5116	0.7255	0.0585	0.077*
C4	0.4516 (5)	0.8519 (3)	0.1903 (4)	0.0593 (8)
C5	0.5270 (6)	0.9545 (3)	0.2290 (4)	0.0689 (10)
H5	0.4567	0.9941	0.2998	0.083*
C6	0.7040 (5)	0.9972 (3)	0.1631 (4)	0.0695 (9)
H6	0.7532	1.0659	0.1882	0.083*
C7	0.0126 (6)	0.6853 (3)	0.2753 (4)	0.0717 (9)
H7	−0.0511	0.7305	0.3429	0.086*
C8	−0.0884 (6)	0.5852 (3)	0.2375 (4)	0.0742 (10)
H8	−0.0170	0.5393	0.1747	0.089*
C9	−0.2781 (6)	0.5539 (3)	0.2868 (4)	0.0757 (10)
H9	−0.3443	0.6017	0.3497	0.091*
C10	−0.3973 (6)	0.4540 (3)	0.2553 (4)	0.0781 (11)
C11	−0.3260 (8)	0.3749 (4)	0.1614 (5)	0.0973 (13)
H11	−0.1919	0.3827	0.1184	0.117*
C12	−0.4506 (11)	0.2854 (4)	0.1313 (6)	0.1188 (19)
H12	−0.4012	0.2338	0.0664	0.143*
C13	−0.6461 (12)	0.2703 (5)	0.1945 (7)	0.128 (2)
H13	−0.7300	0.2094	0.1724	0.153*
C14	−0.7170 (8)	0.3456 (5)	0.2905 (7)	0.1205 (19)
H14	−0.8479	0.3346	0.3363	0.145*
C15	−0.5968 (7)	0.4385 (4)	0.3210 (5)	0.0968 (13)
H15	−0.6488	0.4901	0.3849	0.116*
H2A	0.205 (5)	0.852 (2)	0.323 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0786 (17)	0.127 (2)	0.1032 (19)	−0.0004 (17)	0.0351 (16)	−0.0009 (18)
O2	0.104 (2)	0.104 (2)	0.109 (2)	−0.040 (2)	0.0197 (18)	−0.0008 (18)
N1	0.068 (2)	0.094 (3)	0.0691 (19)	−0.012 (2)	0.0059 (17)	0.008 (2)
N2	0.0610 (19)	0.070 (2)	0.077 (2)	−0.0064 (16)	0.0103 (16)	−0.0075 (15)
N3	0.0674 (19)	0.0658 (19)	0.082 (2)	−0.0096 (16)	0.0027 (17)	0.0023 (16)
C1	0.0512 (18)	0.070 (2)	0.0578 (19)	−0.0043 (18)	0.0033 (16)	0.0044 (17)
C2	0.069 (2)	0.069 (2)	0.062 (2)	0.0083 (19)	0.0106 (19)	−0.0015 (18)
C3	0.062 (2)	0.055 (2)	0.076 (2)	0.0008 (18)	0.0037 (19)	−0.0048 (19)
C4	0.0539 (19)	0.064 (2)	0.0598 (19)	−0.0012 (17)	0.0007 (17)	0.0004 (17)
C5	0.061 (2)	0.072 (2)	0.074 (2)	−0.0022 (18)	0.0110 (19)	−0.0102 (19)
C6	0.067 (2)	0.065 (2)	0.076 (2)	−0.011 (2)	0.0021 (19)	−0.0015 (19)
C7	0.062 (2)	0.075 (2)	0.077 (2)	−0.007 (2)	0.0044 (19)	0.0044 (19)
C8	0.074 (2)	0.068 (2)	0.080 (3)	−0.008 (2)	0.000 (2)	0.0086 (19)
C9	0.077 (3)	0.074 (2)	0.076 (2)	−0.016 (2)	−0.003 (2)	0.0047 (19)
C10	0.073 (3)	0.080 (3)	0.079 (3)	−0.018 (2)	−0.014 (2)	0.018 (2)
C11	0.123 (3)	0.086 (3)	0.082 (3)	−0.024 (3)	−0.002 (3)	−0.001 (2)
C12	0.169 (6)	0.082 (3)	0.102 (4)	−0.034 (4)	−0.022 (4)	0.011 (3)
C13	0.157 (6)	0.098 (4)	0.122 (4)	−0.061 (4)	−0.042 (4)	0.025 (4)
C14	0.096 (3)	0.119 (4)	0.144 (5)	−0.045 (4)	−0.022 (3)	0.045 (4)
C15	0.077 (3)	0.093 (3)	0.119 (3)	−0.014 (3)	−0.009 (3)	0.019 (2)

Geometric parameters (Å, º) top

O1—N1	1.221 (4)	C7—C8	1.423 (5)
O2—N1	1.228 (4)	C7—H7	0.9300
N1—C1	1.438 (4)	C8—C9	1.322 (5)
N2—C4	1.365 (4)	C8—H8	0.9300
N2—N3	1.366 (4)	C9—C10	1.461 (5)
N2—H2A	0.89 (3)	C9—H9	0.9300
N3—C7	1.284 (4)	C10—C11	1.384 (6)
C1—C2	1.373 (4)	C10—C15	1.397 (5)
C1—C6	1.382 (4)	C11—C12	1.368 (6)
C2—C3	1.361 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.364 (8)
C3—C4	1.388 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.362 (8)
C4—C5	1.396 (4)	C13—H13	0.9300
C5—C6	1.369 (4)	C14—C15	1.389 (7)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300

O1—N1—O2	122.2 (3)	N3—C7—H7	119.7
O1—N1—C1	119.5 (4)	C8—C7—H7	119.7
O2—N1—C1	118.3 (3)	C9—C8—C7	123.6 (4)
C4—N2—N3	119.9 (3)	C9—C8—H8	118.2
C4—N2—H2A	120 (2)	C7—C8—H8	118.2
N3—N2—H2A	120 (2)	C8—C9—C10	128.4 (4)
C7—N3—N2	116.7 (3)	C8—C9—H9	115.8
C2—C1—C6	120.5 (3)	C10—C9—H9	115.8
C2—C1—N1	119.6 (3)	C11—C10—C15	118.2 (4)
C6—C1—N1	119.9 (3)	C11—C10—C9	123.7 (4)
C3—C2—C1	120.1 (3)	C15—C10—C9	118.1 (4)
C3—C2—H2	120.0	C12—C11—C10	120.7 (5)
C1—C2—H2	120.0	C12—C11—H11	119.6
C2—C3—C4	120.7 (3)	C10—C11—H11	119.6
C2—C3—H3	119.7	C13—C12—C11	121.2 (5)
C4—C3—H3	119.7	C13—C12—H12	119.4
N2—C4—C3	122.5 (3)	C11—C12—H12	119.4
N2—C4—C5	118.6 (3)	C14—C13—C12	119.2 (5)
C3—C4—C5	118.8 (3)	C14—C13—H13	120.4
C6—C5—C4	120.3 (3)	C12—C13—H13	120.4
C6—C5—H5	119.9	C13—C14—C15	121.0 (6)
C4—C5—H5	119.9	C13—C14—H14	119.5
C5—C6—C1	119.7 (3)	C15—C14—H14	119.5
C5—C6—H6	120.2	C14—C15—C10	119.6 (5)
C1—C6—H6	120.2	C14—C15—H15	120.2
N3—C7—C8	120.7 (4)	C10—C15—H15	120.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.89 (3)	2.20 (3)	3.082 (4)	169 (3)

Symmetry code: (i) x−1, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O₂
M_r	267.28
Crystal system, space group	Monoclinic, Pc
Temperature (K)	296
a, b, c (Å)	6.1011 (3), 12.4505 (6), 9.0076 (4)
β (°)	93.273 (3)
V (Å³)	683.12 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.980, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	5992, 1502, 783
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 0.95
No. of reflections	1502
No. of parameters	185
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.10

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.89 (3)	2.20 (3)	3.082 (4)	169 (3)

Symmetry code: (i) x−1, −y+2, z+1/2.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1531

doi:10.1107/S1600536808021429

Open

access